Best Vacation Homes in Maidstone
New
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
16 Guests
2085 ft²
Private Pool
Fireplace/Heating
Pool
Balcony/Terrace
AU $1,119/Night
7 Nights - AU $7,830
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1539.24 ft²
Oceanfront
Hot Tub- Fireplace/Heating
- Pool
AU $413/Night
7 Nights - AU $2,891
House
10.0(2 Reviews)
1 Bedroom
1 Bath
Ocean View- Balcony/Terrace
View
Pet Friendly
AU $1,079/Night
7 Nights - AU $7,551
New
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $226/Night
7 Nights - AU $1,578
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
13 Guests
- Hot Tub
Parking
Air Conditioner
Internet
AU $352/Night
7 Nights - AU $2,467
New
Condo
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
Kitchen- Parking
AU $2,354/Night
7 Nights - AU $16,481
New
House
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
AU $882/Night
7 Nights - AU $6,174
House
4 Bedrooms
2 Baths
12 Guests
1820 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $867/Night
7 Nights - AU $6,070
Maidstone Luxury Rentals
New
House
1 Bedroom
2 Baths
13 Guests
2034.38 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $6,977/Night
7 Nights - AU $48,842
AU $4,401/Night
7 Nights - AU $30,809
House
3 Bedrooms
2 Baths
6 Guests
1196 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
AU $4,208/Night
7 Nights - AU $29,457
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $4,026/Night
7 Nights - AU $28,180
House
10.0(9 Reviews)
7 Bedrooms
5 Baths
28 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $2,594/Night
7 Nights - AU $18,156
House
10.0(3 Reviews)
7 Bedrooms
5 Baths
28 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $2,588/Night
7 Nights - AU $18,117
House
9.6(9 Reviews)
5 Bedrooms
4 Baths
20 Guests
1866 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
AU $2,503/Night
7 Nights - AU $17,522
House
1 Bedroom
2 Baths
10 Guests
1593.06 ft²
- Private Pool
- Fireplace/Heating
- Pool
- View
AU $2,079/Night
7 Nights - AU $14,552
Maidstone Pet Friendly Vacation Rentals
House
3 Bedrooms
3 Baths
9 Guests
1643 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $625/Night
7 Nights - AU $4,372
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1302.43 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Pool
AU $653/Night
7 Nights - AU $4,573
Villa
8.4(5 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $110/Night
7 Nights - AU $769
New
House
3 Bedrooms
2 Baths
6 Guests
1626 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
AU $455/Night
7 Nights - AU $3,186
Villa
10.0(1 Review)
9 Bedrooms
5 Baths
20 Guests
10763.91 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
AU $996/Night
7 Nights - AU $6,972
New
House
2 Bedrooms
3 Baths
6 Guests
900 ft²
- Oceanfront
- Ocean View
- View
- Pet Friendly
AU $420/Night
7 Nights - AU $2,937
New
House
3 Bedrooms
3 Baths
6 Guests
1412 ft²
- Oceanfront
- Pool
- Ocean View
- View
AU $328/Night
7 Nights - AU $2,294
New
Apartment
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
AU $184/Night
7 Nights - AU $1,291
Maidstone Large Vacation Homes
New
House
4 Bedrooms
2 Baths
10 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $708/Night
7 Nights - AU $4,955
Villa
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1194.79 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
AU $364/Night
7 Nights - AU $2,548
House
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
AU $867/Night
7 Nights - AU $6,066
Villa
10.0(9 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $197/Night
7 Nights - AU $1,380
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
12 Guests
1948.27 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
AU $1,116/Night
7 Nights - AU $7,815
Villa
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
910 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
AU $190/Night
7 Nights - AU $1,333
Villa
10.0(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
1050 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $207/Night
7 Nights - AU $1,451
Villa
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $189/Night
7 Nights - AU $1,324
Why Choose Rent By Owner for your Maidstone Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Maidstone
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the shoulder seasons when this destination offers pleasant weather and fewer crowds, ensuring a relaxing experience in this welcoming region.
Peak Season Highlights
Winter (December to February)
During the winter months, the area experiences mild and pleasant weather, making it an ideal time to visit for those seeking escape from colder climates.
Average Temperature Daytime: 68°F - Nighttime: 50°F
Spring (March to May)
Spring brings warm temperatures and blooming scenery, attracting visitors looking to enjoy outdoor activities and scenic views in this destination.
Average Temperature Daytime: 78°F - Nighttime: 60°F
Off-Season Highlights
Summer (June to August)
The summer months tend to be hotter and more humid, but this is also when you'll find fewer crowds and more affordable vacation rentals available here.
Average Temperature Daytime: 88°F - Nighttime: 72°F
Fall (September to November)
Fall offers cooler temperatures and less tourist activity, providing a peaceful atmosphere for those booking vacation rentals in this region.
Average Temperature Daytime: 75°F - Nighttime: 58°F
Weekly Weather Forecast for Maidstone
How to Book Your Maidstone Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Maidstone
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor grilling with a private barbecue area to savor local flavors.
- Relax by a sparkling swimming pool designed for both leisure and exercise.
- Take advantage of spacious patios or decks perfect for entertaining or unwinding.
- Explore lush gardens or landscaped yards that showcase the region's natural beauty.
- Make use of outdoor dining spaces to enjoy meals while soaking in the fresh air.
- Utilize shaded lounging areas for relaxing in the warm Florida sunshine.
- Access private outdoor sports courts, such as tennis or volleyball, suitable for active guests.
Top Attractions Around Maidstone
What attractions are nearby?
Nearby in this destination, you can enjoy a variety of outdoor activities, explore local parks, or indulge in water sports just moments from your vacation rental in the area.
Family Activities
- Pinellas Trail: Explore this scenic trail perfect for family bike rides and walks, offering a safe outdoor activity in the area.
- Seminole City Park: Enjoy a day of picnicking, playground fun, and outdoor sports in this family-friendly park close to your vacation rental.
- John R. Bonner Nature Park: Discover the natural beauty of Seminole with easy hiking trails and wildlife viewing opportunities suitable for all ages.
- Bayou Liberty Boat Tours: Experience the region from the water on guided boat tours that showcase local wildlife and scenic views ideal for families staying here.
Adult Activities
- Golfing at Seminole Lake Golf Course: Enjoy a day on the greens at this renowned golf course, perfect for relaxing and challenging your skills in the area.
- Exploring local art galleries and shops: Discover unique art pieces and handcrafted goods in the charming shops that showcase the creative spirit of this destination.
- Relaxing at Seminole City Park: Unwind and unwind by strolling through scenic trails or enjoying picnic areas in this popular park nearby.
- Fishing at nearby lakes and waterways: Cast your line in the region’s serene lakes and waterways, offering excellent opportunities for freshwater fishing enthusiasts.
Maidstone Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take advantage of nearby parks and beaches to enjoy the natural beauty that makes this destination a perfect spot for outdoor activities.
- Plan Your Dining Experiences: Discover local eateries and waterfront restaurants to savor regional flavors and make your stay more memorable.
- Utilize Transportation Options: Use local shuttle services or rent a vehicle to easily access attractions and explore the area at your own pace.
- Book Early for Popular Seasons: Secure your preferred vacation rentals well in advance during peak travel seasons to ensure a seamless and enjoyable experience.
Transportation Options
- Seminole Gulf Breeze Transit: This regional bus service offers convenient transportation options for exploring the area and accessing nearby destinations from here.
- PINELLAS SUNCOAST Transit Authority (PSTA): The local public transit system provides reliable bus routes throughout the region, making it easy to get around without a car.
- Rental Car Services: Several rental agencies operate in the vicinity, giving you flexible options for exploring this destination at your own pace.
- Taxi and Rideshare Options: Taxis and rideshare services are readily available here, providing quick and dependable transportation for short trips around the region.
Local Customs Options
- Greeting Etiquette: Visitors are often welcomed with friendly gestures and polite conversation, reflecting the region’s warm hospitality.
- Local Dining Customs: It's customary to enjoy fresh seafood and southern-style dishes, which are staple aspects of dining here in this part of Florida.
- Community Events: Attending neighborhood festivals and outdoor gatherings is a common way for locals to celebrate their community and culture.
- Respect for Nature: The area emphasizes eco-friendly practices and respect for the natural surroundings, important when exploring outdoor activities or local parks.
Frequently Asked Questions About Maidstone?
1. What are the top vacation rentals in Maidstone?
There are a lot of options in Maidstone. If you plan on staying in the Maidstone area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Maidstone:
- UPDATED REMODELED CONDO- NO STAIRS 3 MILES TO THE BEACH! PETS ok! HEATED POOL !
- SUNNY DELIGHT! pets ok! UPDATED HEATED POOL VACATION CONDO. Safe gated community
- Gorgeous Heated Pool House Near Gulf Beaches!
- Professional cottage on 1/2 acre lot in quiet country setting
- SHEEK & GLAM VACATION BEACH CONDO! HEATED POOL,GYM, TENNIS, 1st FLOOR CONDO
- Newly Renovated Close to Beaches Firepit
- Pool Home with Pool Heater and Hot Tub Near Clearwater and other Fine Beaches.
- sleeps 8 people/Beach 5 min./backs on nature park & lake with trails
- Gorgeous private heated pool house, short drive to the beach!
- HOME SWEET HOME!☀️ HUGE HOT TUB. HEATED POOL! 7 miles to beach 4BD 2BA updated!
2. How many vacation rentals have private pools in Maidstone?
There are 297 vacation rentals with private pools near Maidstone. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Maidstone are best for families?
If you are looking for a family-friendly vacation home in Maidstone, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Maidstone:
4. How many Rentbyowner vacation rentals are available in Maidstone?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 882 in the Maidstone area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Maidstone.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so it’s best to review the specific listing details. Many owners offer flexible options, but some may have stricter terms. Be sure to check the individual property's policy before booking.
6. How do I confirm my reservation and what are the payment requirements?
Reservations are typically confirmed through the booking platform once you complete the payment process. Payment methods depend on the owner or listing platform, but secure online transactions are standard. Always verify the details directly with the host if you have questions.
7. Are there any house rules or restrictions I should be aware of before booking?
Yes, each vacation rental will have its own set of house rules, which can include pet policies, smoking restrictions, or maximum occupancy. To ensure a smooth stay, review these rules on the listing page or contact the owner for clarification.
8. What amenities are typically available in vacation rentals here?
Most properties include essential amenities such as Wi-Fi, kitchen facilities, air conditioning, and parking. Additional features like pools, outdoor spaces, or laundry may vary, so it's advisable to check the specific listing for details.
9. How can I contact the property owner if I have questions about my stay?
You can usually reach out to the property owner directly through the messaging system provided on the booking platform. For urgent inquiries or special requests, contact details are often available on the listing or after your reservation is confirmed.
Maidstone Top Rated Vacation Rentals
Condo
10.0(101 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $284/Night
7 Nights - AU $1,987
Condo
10.0(101 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $274/Night
7 Nights - AU $1,919
House
10.0(100 Reviews)
4 Bedrooms
1 Bath
10 Guests
924 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $371/Night
7 Nights - AU $2,597
Condo
10.0(75 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $302/Night
7 Nights - AU $2,116
House
10.0(54 Reviews)
3 Bedrooms
2 Baths
6 Guests
1000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $414/Night
7 Nights - AU $2,901
House
10.0(36 Reviews)
3 Bedrooms
2 Baths
6 Guests
1600 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $394/Night
7 Nights - AU $2,756
House
10.0(32 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
AU $749/Night
7 Nights - AU $5,247
House
10.0(29 Reviews)
3 Bedrooms
2 Baths
8 Guests
1400 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $382/Night
7 Nights - AU $2,671
